Demo

Head of Talent at AI-native insurance startup backed by Founders Fund & Lightspeed

Jack & Jill
San Francisco, CA Full Time
POSTED ON 5/25/2026
AVAILABLE BEFORE 6/23/2026
This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Head of Talent

Salary

Not Disclosed

Company Description

Founders Fund and Lightspeed-backed AI startup transforming the $280B P&C insurance market

Job Description

As the first dedicated talent hire, you will build the recruiting function from scratch for an AI-native company already at multi-7-figure ARR. You'll partner with the founding team to scale an elite group of engineers and researchers from 20 to 100 , defining the culture and organizational design of a generational insurance-tech platform.

Location

San Francisco, USA

Why this role is remarkable

  • Partner directly with founders from Palantir and top trading firms to scale an elite, high-intensity team from 20 to 100 people.
  • Backed by premier investors including Founders Fund, Lightspeed, and Emergence Capital with exceptional product-market fit and multi-7-figure revenue in year one.
  • High-impact founding equity stake in a company replacing legacy fax-and-spreadsheet systems with end-to-end AI claims processing for a massive $280B industry.

What You Will Do

  • Own the full recruiting lifecycle from sourcing to closing world-class technical talent from top AI labs, trading firms, and tier-1 tech companies.
  • Design and implement the entire talent infrastructure, including interview processes, compensation frameworks, and organizational design strategies from the ground up.
  • Serve as a strategic talent advisor to the leadership team, ensuring every hire maintains the company's bar for elite technical excellence and high-ownership culture.

The ideal candidate

  • Proven track record of building or significantly scaling a talent function at an early-stage startup, ideally during the 20 to 100 employee growth phase.
  • Exceptional ability to source and close elite technical talent, specifically engineers and AI researchers who typically gravitate toward top-tier labs or high-frequency trading firms.
  • Thrives in a high-intensity, in-person SF environment and possesses the strategic mindset to build systems without a playbook while moving at extreme startup speed.

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

Next steps

Step 1. Visit the job listing.

Step 2. Click 'Talk to Jack', or go straight there: https://www.jackandjill.ai/jobs/head-of-talent-at-ai-native-insurance-startup-backed-by-founders-fund-and-lights-30b70702-c7e3-4f9a-b9fc-acc64b85f568?utm_source=linkedin&utm_medium=job_post&utm_campaign=featured_role_30b70702-c7e3-4f9a-b9fc-acc64b85f568

Step 3. Talk to Jack so he can understand your experience and ambitions.

Step 4. Jack will make sure Jill (the AI agent working for the company) considers you for this role.

Step 5. If Jill thinks you're a great fit and her client wants to meet you, they will make the introduction.

Step 6. If not, Jack will find you excellent alternatives. All for free.

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.

Salary.com Estimation for Head of Talent at AI-native insurance startup backed by Founders Fund & Lightspeed in San Francisco, CA
$70,650 to $86,302
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Head of Talent at AI-native insurance startup backed by Founders Fund & Lightspeed?

Sign up to receive alerts about other jobs on the Head of Talent at AI-native insurance startup backed by Founders Fund & Lightspeed career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$95,697 - $123,113
Income Estimation: 
$131,357 - $193,022
Income Estimation: 
$120,763 - $148,970
Income Estimation: 
$117,414 - $153,024
Income Estimation: 
$61,308 - $77,964
Income Estimation: 
$95,396 - $131,741
Income Estimation: 
$73,702 - $93,306
Income Estimation: 
$103,427 - $139,931
Income Estimation: 
$78,608 - $102,980
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Jack & Jill

  • Jack & Jill York, NY
  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The ... more
  • Just Posted

  • Jack & Jill York, NY
  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The ... more
  • Just Posted

  • Jack & Jill San Francisco, CA
  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The ... more
  • Just Posted

  • Jack & Jill San Francisco, CA
  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The ... more
  • Just Posted


Not the job you're looking for? Here are some other Head of Talent at AI-native insurance startup backed by Founders Fund & Lightspeed jobs in the San Francisco, CA area that may be a better fit.

  • Jack & Jill San Francisco, CA
  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The ... more
  • 2 Days Ago

  • Jack & Jill San Francisco, CA
  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The ... more
  • 11 Days Ago

AI Assistant is available now!

Feel free to start your new journey!